Active Compound Combinations Having Insecticidal And Acaricidal Properties

ABSTRACT

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which
 
R 1  and A have the meanings given in the description
 
and, secondly, at least one further known active compound from the class of the pyrethroids, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids.

The present invention relates to novel active compound combinationscomprising, firstly, at least one known compound of the formula (I) and,secondly, at least one further known active compound from the class ofthe pyrethroids, which combinations are highly suitable for controllinganimal pests such as insects and unwanted acarids. The invention alsorelates to methods for controlling animal pests on plants and seed, tothe use of the active compound combinations according to the inventionfor treating seed, to a method for protecting seed and last but notleast to the seed treated with the active compound combinationsaccording to the invention.

It is already known that compounds of the formula (I)

in which

A represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which isoptionally substituted in the 6-position by fluorine, chlorine, bromine,methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-ylwhich is optionally substituted in the 6-position by chlorine or methylor represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl orrepresents 1,3-thiazol-5-yl which is optionally substituted in the2-position by chlorine or methyl, or

A represents a pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl,1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolylradical which is optionally substituted by fluorine, chlorine, bromine,cyano, nitro, C₁-C₄-alkyl (which is optionally substituted by fluorineand/or chlorine), C₁-C₃-alkylthio (which is optionally substituted byfluorine and/or chlorine) or C₁-C₃-alkylsulphonyl (which is optionallysubstituted by fluorine and/or chlorine),

or

A represents a radical

in which

X represents halogen, alkyl or haloalkyl,

Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano and

R¹ represents alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy, alkoxyalkyl orhalocycloalkylalkyl,

have insecticidal action (cf. EP 0 539 588, WO 2007/115643 A1, WO2007/115644 A1 and WO 2007/115646 A1).

Furthermore, it is known that certain active compounds from the class ofthe pyrethroids have insecticidal and acaricidal properties. Thesecompounds have been disclosed in published patent specifications andscientific publications. Most of the insecticidal compounds describedherein from the class of the pyrethroids are commercially available asindividual active compounds in compositions for controlling animalpests. These compounds and compositions have been described in handbookssuch as “The Pesticide Manual, 14th edition, C. D. S. Thomlin (Ed.),British Crop Protection Council, Surrey, UK, 2006”, which is herebyincorporated by reference with respect to most of the active compoundsdisclosed herein from the class of the organophosphates or carbamates.The active compounds which are neither commercially available nor listedin the “Pesticide Manual” are identified by IUPAC number and/orstructural formula.

The activity of the insecticidal compounds of the formula (I) or theactive compound from the class of the pyrethroids is generally good.However, in particular at low application rates and in the case ofcertain pests, they do not always meet the demands of agriculturalpractice, and there is still a need for economically efficient andecologically safe pest control.

Further demands on insecticidal compounds include the reduction of thedosage rate; a substantial broadening of the spectrum of pests that canbe controlled, including resistant pests; increased safety in use;reduced phytotoxicity and thus better tolerance by plants; the controlof pests in their different development stages; better behaviour duringproduction of the insecticidal compounds, for example during grinding ormixing, during their storage or during their use; a very advantageousbiocidal spectrum, even at low concentrations, with associated goodcompatibility with warm-blooded organisms, fish and plants; andachievement of an additional effect, for example an algicidal,anthelmintic, avicidal, bactericidal, fungicidal, molluscicidal,nematicidal, plant-activating, rodenticidal or virucidal action.

Further specific demands on insecticidal compounds to be used onvegetative and generative plant propagation material include negligiblephytotoxicity when applied to the seed and plant propagation material,compatibility with soil conditions (for example with regard to bindingof the compound to the soil), systemic activity in the plant, nonegative impact on germination, and efficacy during the lifecycle of thepest in question.

The object of the invention is to meet one or more of the demandsmentioned above, such as, for example, the reduction of the dosage rate,a broadening of the spectrum of pests that can be controlled, includingresistant pests, and in particular the specific demands for theapplicability on vegetative and generative plant propagation material.

It has now been found that combinations of at least one compound of theformula (I), with the proviso that4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one areexcluded, and at least one compound selected from the group consistingof

1. acrinathrin

-   -   known from EP-A-048 186,        2. alpha-cypermethrin

-   -   known from EP-A-067 461,        3. beta-cyfluthrin

-   -   known from EP-A-206 149,        4. gamma-cyhalothrin

-   -   known from DE-A-2 802 962,        5. cypermethrin

-   -   known from DE-A-2 326 077,        6. deltamethrin

-   -   known from DE-A-2 326 077,        7. esfenvalerate

-   -   known from DE-A-2 737 297,        8. ethofenprox

-   -   known from DE-A-3 117 510,        9. fenpropathrin

-   -   known from DE-A-2 231 312,        10. fenvalerate

-   -   known from DE-A-2 335 347,        11. flucythrinate

-   -   known from DE-A-2 757 066,        12. lambda-cyhalothrin

-   -   known from EP-A-106 469,        13. permethrin

-   -   known from DE-A-2 326 077,        14. tau-fluvalinate

-   -   known from EP-A-038 617,        15. tralomethrin

-   -   known from DE-A-2 742 546,        16. zeta-cypermethrin

-   -   known from EP-A-026 542,        17. cyfluthrin

-   -   known from DE-A-27 09 264,        18. bifenthrin

-   -   known from EP-A-049 977,        19. cycloprothrin

-   -   known from DE-A-2653189,        20. eflusilanate

-   -   known from DE-A-36 04 781,        21. fubfenprox

-   -   known from DE-A-37 08 231,        22. pyrethrin

-   -   R=CH₃ or —CO₂CH₃    -   R₁=—CH═CH₂ or —CH₃ or —CH₂CH₃    -   known from The Pesticide Manual, 1997, 11. Edition, p. 1056,        23. resmethrin

-   -   known from GB-A-1 168 797,        and        24. tefluthrin

-   -   known from EP-A131 199        25. transfluthrin (known from EP 2 79 325)

-   -   are synergistically active and are suitable for controlling        animal pests.

Surprisingly, the insecticidal action of the active compoundcombinations according to the invention considerably exceeds the totalof the actions of the individual active compounds. A true synergisticeffect which could not have been predicted exists, not just acomplementation of action.

The synergistic action of the active compound combinations according tothe invention of a compound of the formula (I) and an active compoundfrom the class of the pyrethroids broadens the range of action of thecompound of the formula (I) and the active compound from the class ofthe pyrethroids primarily by a reduction of the dosage rate and bybroadening the spectrum of pests that can be controlled. Thus, using theactive compound combination according to the invention of a compound ofthe formula (I) and an active compound from the class of thepyrethroids, it is still possible to achieve a high degree of pestcontrol, even in cases where the individual compounds of the activecompound combinations according to the invention have only insufficientactivity at the low application rates used.

In addition to the synergistic action described above, the activecompound combinations according to the invention may show othersurprising advantages including increased safety in use; reducedphytotoxicity and thus better tolerance by plants; the control of pestsin their different development stages; better behaviour duringproduction of the insecticidal compounds, for example during grinding ormixing, during their storage or during their use; a very advantageousbiocidal spectrum, even at low concentrations, with associated goodcompatibility with warm-blooded organisms, fish and plants; andachievement of an additional effect, for example an algicidal,anthelmintic, avicidal, bactericidal, fungicidal, molluscicidal,nematicidal, plant-activating, rodenticidal or virucidal action.

Furthermore, surprisingly, it has been found that the active compoundcombinations according to the invention are particularly suitable forprotecting seeds and/or seedlings and leaves from a plant grown from theseeds against damage by pests. Thus, the active compound combinationsaccording to the invention have negligible phytotoxicity when applied tothe plant propagation material, compatibility with soil conditions (forexample with regard to binding of the compound to the soil), systemicactivity in the plant, no negative impact on germination, and efficacyduring the life cycle of the pest in question.

The active compound combinations according to the invention comprise, inaddition to at least one compound of the formula (I), one of thepyrethroids 1 to 25 listed individually above. The active compoundcombinations according to the invention preferably comprise exactly onecompound of the formula (I) and exactly one of the pyrethroids 1 to 25listed individually above. Preference is furthermore given to activecompound combinations comprising one compound of the formula (I) and twocompounds of the pyrethroids 1 to 25 listed individually above.Preference is furthermore given to mixtures comprising two compounds ofthe formula (I) and one compound of the pyrethroids 1 to 25 listedindividually above.

The invention also comprises active compound combinations comprising acompound of the formula (I) and a pyrethroid selected from the groupconsisting of the pyrethroids ester insecticides aliethrin,bioallethrin, barthrin, bioethanomethrin, cyclethrin, cyphenothrin,dimefluthrin, dimethrin, empenthrin, fenfluthrin, fenpyrithrin,flubrocythrinate, flumethrin, furethrin, imiprothrin, metofluthrin,phenothrin, prallethrin, profluthrin, pyresmethrin, terallethrin andtetramethrin; the silicon-containing insecticide eflusilanate, thepyrethroid ether insecticides halfenprox and protrifenbute; and thepyrethrines (botanical insecticides) cinerin I and II, jasmolin I and IIand pyrethrin I and II.

Preferred sub-groups of the compounds of the formula (I) mentioned abovein the active compound combinations according to the invention with atleast one of the pyrethroids 1 to 25 listed individually above arelisted below, with the proviso that4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)-amino}furan-2(5H)-one areexcluded.

A preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl,6-bromopyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethylpyrid-3-yl,6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or2-methyl-1,3-thiazol-5-yl, 2-chloro-pyrimidin-5-yl,2-trifluoromethylpyrimidin-5-yl, 5,6-difluoropyrid-3-yl,5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl,5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl,5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl,5-chloro-6-bromopyrid-3-yl, 5,6-dibromo-pyrid-3-yl,5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl,5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl,5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl,5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl,5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-ylor 5-difluoromethyl-6-iodopyrid-3-yl.

R¹ preferably represents optionally fluorine-substituted C₁-C₅-alkyl,C₂-C₅-alkenyl, C₃-C₅-cycloalkyl, C₃-C₅-cycloalkylalkyl or C₁-C₅-alkoxy.

A particularly preferably represents the 6-fluoropyrid-3-yl,6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,2-chloro-1,3-thiazol-5-yl, 2-chloropyrimidin-5-yl,5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl,5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl,5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl,5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or5-difluoromethyl-6-chloropyrid-3-yl radical.

R¹ particularly preferably represents methyl, methoxy, ethyl, propyl,vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethylor 2-fluorocyclopropyl.

A very particularly preferably represents the 6-fluoropyrid-3-yl,6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,2-chloro-1,3-thiazol-5-yl or 5,6-dichloropyrid-3-yl radical.

R¹ very particularly preferably represents methyl, cyclopropyl, methoxy,2-fluoroethyl or 2,2-difluoroethyl.

A most preferably represents the 6-chloropyrid-3-yl or5-fluoro-6-chloropyrid-3-yl radical.

R¹ most preferably represents methyl, 2-fluoroethyl or2,2-difluoroethyl.

In a special group of compounds of the formula (I), A represents6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I), A represents6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I), A represents6-chloro-1,4-pyridazin-3-yl.

In a further special group of compounds of the formula (I), A represents2-chloro-1,3-thiazol-5-yl.

In a further special group of compounds of the formula (I), A represents5-fluoro-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I), A represents5-fluoro-6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I), A represents5,6-dichloropyrid-3-yl.

In a further special group of compounds of the formula (I), R¹represents methyl.

In a further special group of compounds of the formula (I), R¹represents ethyl.

In a further special group of compounds of the formula (I), R¹represents cyclopropyl.

In a further special group of compounds of the formula (I), R¹represents 2-fluoroethyl.

In a further special group of compounds of the formula (I), R¹represents 2,2-difluoroethyl.

The abovementioned general or preferred radical definitions orillustrations can be combined with one another as desired, i.e.including combinations between the respective preferred ranges.

Preference according to the invention is given to compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to compoundsof the formula (I) which contain a combination of the meanings listedabove as being particularly preferred.

Very particular preference according to the invention is given tocompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

A preferred sub-group of the compounds of the formula (I) are those ofthe formula (I-a)

in which

B represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which isoptionally substituted in the 6-position by fluorine, chlorine, bromine,methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-ylwhich is optionally substituted in the 6-position by chlorine, or methylor represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl orrepresents 1,3-thiazol-5-yl which is optionally substituted in the2-position by chlorine or methyl,

R² represents haloalkyl, haloalkenyl, halocycloalkyl orhalocycloalkylalkyl.

Preferred substituents or ranges of the radicals mentioned in theformula (I-a) shown above and below are illustrated below:

B preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl,6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl,6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or2-methyl-1,3-thiazol-5-yl.

R² preferably represents fluorine-substituted C₁-C₅-alkyl,C₂-C₅-alkenyl, C₃-C₅-cycloalkyl or C₃-C₅-cycloalkylalkyl.

B particularly preferably represents the 6-fluoropyrid-3-yl,6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,2-chloro-1,3-thiazol-5-yl radical.

R² particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl,2-fluorocyclopropyl.

B very particularly preferably represents the 6-chloropyrid-3-ylradical.

R² very particularly preferably represents 2-fluoroethyl or2,2-difluoroethyl.

In a special group of compounds of the formula (I-a), B represents6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-a), Brepresents 6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-a), Brepresents 6-chloro-1,4-pyridazin-3-yl.

In a further special group of compounds of the formula (I-a), R²represents 2-fluoroethyl.

In a further special group of compounds of the formula (I-a), R²represents 2,2-difluoroethyl.

A further preferred sub-group of the compounds of the formula (I) arethose of the formula (I-b)

in which

D represents a radical

in which

X and Y have the meanings given above,

R³ represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy.

Preferred substituents or ranges of the radicals mentioned in theformula (I-b) shown above and below are illustrated below:

D preferably represents one of the radicals 5,6-difluoropyrid-3-yl,5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl,5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl,5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl,5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl,5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl,5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl,5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl,5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl,5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl,5-difluoromethyl-6-iodopyrid-3-yl.

R³ preferably represents C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl orC₃-C₄-cycloalkyl.

D particularly preferably represents 5-fluoro-6-chloropyrid-3-yl,5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl,5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl,5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl,5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.

R³ particularly preferably represents C₁-C₄-alkyl.

D very particularly preferably represents 5-fluoro-6-chloropyrid-3-yl or5-fluoro-6-bromopyrid-3-yl.

R³ very particularly preferably represents methyl, ethyl, propyl, vinyl,allyl, propargyl or cyclopropyl.

D most preferably represents 5-fluoro-6-chloropyrid-3-yl.

R³ most preferably represents methyl or cyclopropyl.

In a further special group of compounds of the formula (I-b), Drepresents 5-fluoro-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5,6-dichloropyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5-bromo-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5-methyl-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5-fluoro-6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5-chloro-6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-b), Drepresents 5-chloro-6-iodopyrid-3-yl.

In a further special group of compounds of the formula (I-b), R³represents methyl.

In a further special group of compounds of the formula (I-b), R³represents ethyl.

In a further special group of compounds of the formula (I-b), R³represents cyclopropyl.

A further preferred sub-group of the compounds of the formula (I) arethose of the formula (I-c)

in which

E represents a radical

in which

X and Y have the meanings given above and

R⁴ represents haloalkyl, haloalkenyl, halocycloalkyl orhalocycloalkylalkyl.

Preferred substituents or ranges of the radicals mentioned in theformula (I-c) shown above and below are illustrated below:

E preferably represents one of the radicals 5,6-difluoropyrid-3-yl,5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl,5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl,5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl,5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl,5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl,5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl,5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl,5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl,5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl,5-difluoromethyl-6-iodopyrid-3-yl.

R⁴ preferably represents fluorine-substituted C₁-C₅-alkyl,C₂-C₅-alkenyl, C₃-C₅-cycloalkyl or C₃-C₅-cycloalkylalkyl.

E particularly preferably represents 2-chloropyrimidin-5-yl,5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl,5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl,5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl,5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or5-difluoromethyl-6-chloropyrid-3-yl.

R⁴ particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl,2-fluorocyclopropyl.

E very particularly preferably represents 5-fluoro-6-chloropyrid-3-yl.

R⁴ very particularly preferably represents 2-fluoroethyl or2,2-difluoroethyl.

In a further special group of compounds of the formula (I-c), Erepresents 5-fluoro-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5,6-dichloropyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5-bromo-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5-methyl-6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5-fluoro-6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5-chloro-6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-c), Erepresents 5-chloro-6-iodopyrid-3-yl.

In a further special group of compounds of the formula (I-c), R⁴represents 2-fluoroethyl.

In a further special group of compounds of the formula (I-c), R⁴represents 2,2-difluoroethyl.

A preferred sub-group of the compounds of the formula (I) are those ofthe formula (I-d)

in which

G represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which isoptionally substituted in the 6-position by fluorine, chlorine, bromine,methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-ylwhich is optionally substituted in the 6-position by chlorine or methylor represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl orrepresents 1,3-thiazol-5-yl which is optionally substituted in the2-position by chlorine or methyl, and

R⁵ represents C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₄-cycloalkyl or C₁-C₄alkoxy, with the proviso that4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl] (cyclopropyl)amino}furan-2(5H)-one areexcluded.

Preferred substituents or ranges of the radicals mentioned in theformula (I-d) shown above and below are illustrated below:

G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl,6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl,6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or2-methyl-1,3-thiazol-5-yl.

R⁵ preferably represents C₁-C₄-alkyl, C₁-alkoxy, C₂-C₄-alkenyl,C₂-C₄-alkynyl or C₃-C₄-cycloalkyl.

G particularly preferably represents the 6-fluoropyrid-3-yl,6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl,2-chloro-1,3-thiazol-5-yl radical.

R⁵ particularly preferably represents methyl, methoxy, ethyl, propyl,vinyl, allyl, propargyl or cyclopropyl.

G very particularly preferably represents the 6-chloropyrid-3-ylradical.

R⁵ very particularly preferably represents methyl or cyclopropyl.

In a special group of compounds of the formula (I-d), G represents6-chloropyrid-3-yl.

In a further special group of compounds of the formula (I-d), Grepresents 6-bromopyrid-3-yl.

In a further special group of compounds of the formula (I-d), Grepresents 6-chloro-1,4-pyridazin-3-yl.

In a further special group of compounds of the formula (I-d), Grepresents 2-chloro-1,3-thiazol-5-yl.

In a further special group of compounds of the formula (I-d), Grepresents 6-fluoropyrid-3-yl.

In a further special group of compounds of the formula (I-d), Grepresents 6-trifluoromethylpyrid-3-yl.

In a further special group of compounds of the formula (I-d), Grepresents 6-fluoropyrid-3-yl.

In a further special group of compounds of the formula (I-d), R⁵represents methyl.

In a further special group of compounds of the formula (I-d), R⁵represents cyclopropyl.

Specific mention may be made of the following compounds of the generalformula (I):

-   -   compound (I-1),        4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115644 A1.

-   -   Compound (I-2),        4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115644 A1.

-   -   Compound (I-3),        4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115644 A1.

-   -   Compound (I-4),        4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115644 A1.

-   -   Compound (I-5),        4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115644 A1.

-   -   Compound (I-6),        4-{[(6-chloro-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115643 A1.

-   -   Compound (I-7),        4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115646 A1.

-   -   Compound (I-8),        4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one,        has the formula

and is known from WO 2007/115643 A1.

The active compound combinations according to the invention preferablycomprise at least one of the compounds of the formula (I) selected fromthe group consisting of the compounds of the formulae (I-a), (I-b),(I-c) and (I-d) shown above, with the proviso that4-{[(6-chloropyrid-3-yl)methyl]methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl](cyclo-propyl)amino}furan-2(5H)-one areexcluded, and one of the pyrethroids 1 to 25 listed individually above.Likewise preferably, the active compound combinations according to theinvention comprise at least one of the compounds of the formula (I) asdefined in the present paragraph and one of the pyrethroids from thegroup consisting of the pyrethroid ester insecticides allethrin,bioallethrin, barthrin, bioethanomethrin, cyclethrin, cyphenothrin,dimefluthrin, dimethrin, empenthrin, fenfluthrin, fenpyrithrin,flubrocythrinate, flumethrin, furethrin, imiprothrin, metofluthrin,phenothrin, prallethrin, profluthrin, pyresmethrin, terallethrin andtetramethrin; the silicon-containing insecticide eflusilanate, thepyrethroid ether insecticides halfenprox and protrifenbute; and thepyrethrines (botanical insecticides) cinerin I and II, jasmolin I and IIand pyrethrin I and II.

The active compound combinations according to the invention furthermorepreferably comprise at least one of the compounds of the formula (I)selected from the group consisting of the compounds of the formulae(I-a), (I-b) and (I-c) shown above and one of the pyrethroids 1 to 25listed individually above. Likewise preferably, the active compoundcombinations according to the invention comprise at least one of thecompounds of the formula (I) as defined in the present paragraph and oneof the pyrethroids from the group consisting of the pyrethroid esterinsecticides allethrin, bioallethrin, barthrin, bioethanomethrin,cyclethrin, cyphenothrin, dimefluthrin, dimethrin, empenthrin,fenfluthrin, fenpyrithrin, flubrocythrinate, flumethrin, furethrin,imiprothrin, metofluthrin, phenothrin, prallethrin, profluthrin,pyresmethrin, terallethrin and tetramethrin; the silicon-containinginsecticide eflusilanate, the pyrethroid ether insecticides halfenproxand protrifenbute; and the pyrethrines (botanical insecticides) cinerinI and II, jasmolin I and II and pyrethrin I and II.

Particularly preferably, the active compound combinations according tothe invention comprise at least one of the compounds of the formula (I)in which A is selected from among the radicals 6-fluoropyrid-3-yl,6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,2-chloro-1,3-thiazol-5-yl and 5,6-dichloropyrid-3-yl and R¹ is selectedfrom among the radicals methyl, cyclopropyl, methoxy, 2-fluoroethyl and2,2-difluoroethyl, with the proviso that4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one areexcluded, and one of the pyrethroids 1 to 25 listed individually above.Likewise preferably, the active compound combinations according to theinvention comprise at least one of the compounds of the formula (I) asdefined in the present paragraph and one of the pyrethroids from thegroup consisting of the pyrethroid ester insecticides allethrin,bioallethrin, barthrin, bioethanomethrin, cyclethrin, cyphenothrin,dimefluthrin, dimethrin, empenthrin, fenfluthrin, fenpyrithrin,flubrocythrinate, flumethrin, furethrin, imiprothrin, metofluthrin,phenothrin, prallethrin, profluthrin, pyresmethrin, terallethrin andtetramethrin; the silicon-containing insecticide eflusilanate, thepyrethroid ether insecticides halfenprox and protrifenbute; and thepyrethrines (botanical insecticides) cinerin I and II, jasmolin I and IIand pyrethrin I and II.

Very particularly preferably, the active compound combinations accordingto the invention comprise at least one compound of the formula (I)selected from the group consisting of the compounds of the formulae(I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7) and (I-8), and one ofthe pyrethroids 1 to 25 listed individually above. Most preferably, theactive compound combinations according to the invention comprise atleast one compound of the formula (I) selected from the group consistingof the compounds of the formulae (I-2), (I-2), (I-3), (I-4), (I-5),(I-6), (I-7) and (I-8), and transfluthrin. Likewise preferably, theactive compound combinations according to the invention comprise atleast one of the compounds of the formula (I) as defined in the presentparagraph and one of the pyrethroids from the group consisting of thepyrethroid ester insecticides allethrin, bioallethrin, barthrin,bioethanomethrin, cyclethrin, cyphenothrin, dimefluthrin, dimethrin,empenthrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flumethrin,furethrin, imiprothrin, metofluthrin, phenothrin, prallethrin,profluthrin, pyresmethrin, terallethrin and tetramethrin; thesilicon-containing insecticide eflusilanate, the pyrethroid etherinsecticides halfenprox and protrifenbute; and the pyrethrines(botanical insecticides) cinerin I and II, jasmolin I and II andpyrethrin I and II.

This gives the combinations listed in Table 1, where each combinationper se is a very particularly preferred embodiment of the invention.

TABLE 1 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 1-1 I-1 and  1(acrinathrin) 1-2 I-1 and  2 (alpha-cypermethrin) 1-3 I-1 and  3(beta-cyfluthrin) 1-4 I-1 and  4 (gamma-cyhalothrin) 1-5 I-1 and  5(cypermethrin) 1-6 I-1 and  6 (deltamethrin) 1-7 I-1 and  7(esfenvalerate) 1-8 I-1 and  8 (ethofenprox) 1-9 I-1 and  9(fenpropathrin) 1-10 I-1 and 10 (fenvalerate) 1-11 I-1 and 11(flucythrinate) 1-12 I-1 and 12 (lambda-cyhalothrin) 1-13 I-1 and 13(permethrin) 1-14 I-1 and 14 (tau-fluvalinate) 1-15 I-1 and 15(tralomethrin) 1-16 I-1 and 16 (zeta-cypermethrin) 1-17 I-1 and 17(cyfluthrin) 1-18 I-1 and 18 (bifenthrin) 1-19 I-1 and 19(cycloprothrin) 1-20 I-1 and 20 (eflusilanate) 1-21 I-1 and 21(fubfenprox) 1-22 I-1 and 22 (pyrethrin) 1-23 I-1 and 23 (resmethrin)1-24 I-1 and 24 (tefluthrin) 1-25 I-1 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 2 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 2 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 2-1 I-2 and  1(acrinathrin) 2-2 I-2 and  2 (alpha-cypermethrin) 2-3 I-2 and  3(beta-cyfluthrin) 2-4 I-2 and  4 (gamma-cyhalothrin) 2-5 I-2 and  5(cypermethrin) 2-6 I-2 and  6 (deltamethrin) 2-7 I-2 and  7(esfenvalerate) 2-8 I-2 and  8 (ethofenprox) 2-9 I-2 and  9(fenpropathrin) 2-10 I-2 and 10 (fenvalerate) 2-11 I-2 and 11(flucythrinate) 2-12 I-2 and 12 (lambda-cyhalothrin) 2-13 I-2 and 13(permethrin) 2-14 I-2 and 14 (tau-fluvalinate) 2-15 I-2 and 15(tralomethrin) 2-16 I-2 and 16 (zeta-cypermethrin) 2-17 I-2 and 17(cyfluthrin) 2-18 I-2 and 18 (bifenthrin) 2-19 I-2 and 19(cycloprothrin) 2-20 I-2 and 20 (eflusilanate) 2-21 I-2 and 21(fubfenprox) 2-22 I-2 and 22 (pyrethrin) 2-23 I-2 and 23 (resmethrin)2-24 I-2 and 24 (tefluthrin) 2-25 I-2 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 3 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 3 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 3-1 I-3 and  1(acrinathrin) 3-2 I-3 and  2 (alpha-cypermethrin) 3-3 I-3 and  3(beta-cyfluthrin) 3-4 I-3 and  4 (gamma-cyhalothrin) 3-5 I-3 and  5(cypermethrin) 3-6 I-3 and  6 (deltamethrin) 3-7 I-3 and  7(esfenvalerate) 3-8 I-3 and  8 (ethofenprox) 3-9 I-3 and  9(fenpropathrin) 3-10 I-3 and 10 (fenvalerate) 3-11 I-3 and 11(flucythrinate) 3-12 I-3 and 12 (lambda-cyhalothrin) 3-13 I-3 and 13(permethrin) 3-14 I-3 and 14 (tau-fluvalinate) 3-15 I-3 and 15(tralomethrin) 3-16 I-3 and 16 (zeta-cypermethrin) 3-17 I-3 and 17(cyfluthrin) 3-18 I-3 and 18 (bifenthrin) 3-19 I-3 and 19(cycloprothrin) 3-20 I-3 and 20 (eflusilanate) 3-21 I-3 and 21(fubfenprox) 3-22 I-3 and 22 (pyrethrin) 3-23 I-3 and 23 (resmethrin)3-24 I-3 and 24 (tefluthrin) 3-25 I-3 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 4 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 4 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 4-1 I-4 and  1(acrinathrin) 4-2 I-4 and  2 (alpha-cypermethrin) 4-3 I-4 and  3(beta-cyfluthrin) 4-4 I-4 and  4 (gamma-cyhalothrin) 4-5 I-4 and  5(cypermethrin) 4-6 I-4 and  6 (deltamethrin) 4-7 I-4 and  7(esfenvalerate) 4-8 I-4 and  8 (ethofenprox) 4-9 I-4 and  9(fenpropathrin) 4-10 I-4 and 10 (fenvalerate) 4-11 I-4 and 11(flucythrinate) 4-12 I-4 and 12 (lambda-cyhalothrin) 4-13 I-4 and 13(permethrin) 4-14 I-4 and 14 (tau-fluvalinate) 4-15 I-4 and 15(tralomethrin) 4-16 I-4 and 16 (zeta-cypermethrin) 4-17 I-4 and 17(cyfluthrin) 4-18 I-4 and 18 (bifenthrin) 4-19 I-4 and 19(cycloprothrin) 4-20 I-4 and 20 (eflusilanate) 4-21 I-4 and 21(fubfenprox) 4-22 I-4 and 22 (pyrethrin) 4-23 I-4 and 23 (resmethrin)4-24 I-4 and 24 (tefluthrin) 4-25 I-4 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 5 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 5 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 5-1 I-5 and  1(acrinathrin) 5-2 I-5 and  2 (alpha-cypermethrin) 5-3 I-5 and  3(beta-cyfluthrin) 5-4 I-5 and  4 (gamma-cyhalothrin) 5-5 I-5 and  5(cypermethrin) 5-6 I-5 and  6 (deltamethrin) 5-7 I-5 and  7(esfenvalerate) 5-8 I-5 and  8 (ethofenprox) 5-9 I-5 and  9(fenpropathrin) 5-10 I-5 and 10 (fenvalerate) 5-11 I-5 and 11(flucythrinate) 5-12 I-5 and 12 (lambda-cyhalothrin) 5-13 I-5 and 13(permethrin) 5-14 I-5 and 14 (tau-fluvalinate) 5-15 I-5 and 15(tralomethrin) 5-16 I-5 and 16 (zeta-cypermethrin) 5-17 I-5 and 17(cyfluthrin) 5-18 I-5 and 18 (bifenthrin) 5-19 I-5 and 19(cycloprothrin) 5-20 I-5 and 20 (eflusilanate) 5-21 I-5 and 21(fubfenprox) 5-22 I-5 and 22 (pyrethrin) 5-23 I-5 and 23 (resmethrin)5-24 I-5 and 24 (tefluthrin) 5-25 I-5 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 6 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 6 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 6-1 I-6 and  1(acrinathrin) 6-2 I-6 and  2 (alpha-cypermethrin) 6-3 I-6 and  3(beta-cyfluthrin) 6-4 I-6 and  4 (gamma-cyhalothrin) 6-5 I-6 and  5(cypermethrin) 6-6 I-6 and  6 (deltamethrin) 6-7 I-6 and  7(esfenvalerate) 6-8 I-6 and  8 (ethofenprox) 6-9 I-6 and  9(fenpropathrin) 6-10 I-6 and 10 (fenvalerate) 6-11 I-6 and 11(flucythrinate) 6-12 I-6 and 12 (lambda-cyhalothrin) 6-13 I-6 and 13(permethrin) 6-14 I-6 and 14 (tau-fluvalinate) 6-15 I-6 and 15(tralomethrin) 6-16 I-6 and 16 (zeta-cypermethrin) 6-17 I-6 and 17(cyfluthrin) 6-18 I-6 and 18 (bifenthrin) 6-19 I-6 and 19(cycloprothrin) 6-20 I-6 and 20 (eflusilanate) 6-21 I-6 and 21(fubfenprox) 6-22 I-6 and 22 (pyrethrin) 6-23 I-6 and 23 (resmethrin)6-24 I-6 and 24 (tefluthrin) 6-25 I-6 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 7 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 7 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 7-1 I-7 and  1(acrinathrin) 7-2 I-7 and  2 (alpha-cypermethrin) 7-3 I-7 and  3(beta-cyfluthrin) 7-4 I-7 and  4 (gamma-cyhalothrin) 7-5 I-7 and  5(cypermethrin) 7-6 I-7 and  6 (deltamethrin) 7-7 I-7 and  7(esfenvalerate) 7-8 I-7 and  8 (ethofenprox) 7-9 I-7 and  9(fenpropathrin) 7-10 I-7 and 10 (fenvalerate) 7-11 I-7 and 11(flucythrinate) 7-12 I-7 and 12 (lambda-cyhalothrin) 7-13 I-7 and 13(permethrin) 7-14 I-7 and 14 (tau-fluvalinate) 7-15 I-7 and 15(tralomethrin) 7-16 I-7 and 16 (zeta-cypermethrin) 7-17 I-7 and 17(cyfluthrin) 7-18 I-7 and 18 (bifenthrin) 7-19 I-7 and 19(cycloprothrin) 7-20 I-7 and 20 (eflusilanate) 7-21 I-7 and 21(fubfenprox) 7-22 I-7 and 22 (pyrethrin) 7-23 I-7 and 23 (resmethrin)7-24 I-7 and 24 (tefluthrin) 7-25 I-7 and 25 (transfluthrin)

Furthermore, the combinations listed in Table 8 are obtained, where eachcombination per se is a preferred embodiment of the invention.

TABLE 8 Active compound combination comprising No. of the activecompound Compound of combination the formula I Pyrethroid 8-1 I-8 and  1(acrinathrin) 8-2 I-8 and  2 (alpha-cypermethrin) 8-3 I-8 and  3(beta-cyfluthrin) 8-4 I-8 and  4 (gamma-cyhalothrin) 8-5 I-8 and  5(cypermethrin) 8-6 I-8 and  6 (deltamethrin) 8-7 I-8 and  7(esfenvalerate) 8-8 I-8 and  8 (ethofenprox) 8-9 I-8 and  9(fenpropathrin) 8-10 I-8 and 10 (fenvalerate) 8-11 I-8 and 11(flucythrinate) 8-12 I-8 and 12 (lambda-cyhalothrin) 8-13 I-8 and 13(permethrin) 8-14 I-8 and 14 (tau-fluvalinate) 8-15 I-8 and 15(tralomethrin) 8-16 I-8 and 16 (zeta-cypermethrin) 8-17 I-8 and 17(cyfluthrin) 8-18 I-8 and 18 (bifenthrin) 8-19 I-8 and 19(cycloprothrin) 8-20 I-8 and 20 (eflusilanate) 8-21 I-8 and 21(fubfenprox) 8-22 I-8 and 22 (pyrethrin) 8-23 I-8 and 23 (resmethrin)8-24 I-8 and 24 (tefluthrin) 8-25 I-8 and 25 (transfluthrin)

If the active compounds are present in the active compound combinationsaccording to the invention in certain weight ratios, the synergisticeffect is particularly pronounced. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range. In general, the combinations accordingto the invention comprise an active compound of the formula (I) and oneof the pyrethroids 1 to 25 listed individually above in the followingpreferred and particularly preferred mixing ratios:

Preferring mixing ratio: 125:1 to 1:125

particularly preferred mixing ratio: 25:1 to 1:25

The mixing ratios are based on weight ratios. The ratio is to beunderstood as meaning compound of the formula (I): pyrethroid. Furthermixing ratios of the compound of the formula (I) to one of thepyrethroids 1 to 25 are specified below and are sorted by increasingpreference of the mixing ratios: 95:1 to 1:95, 95:1 to 1:90, 95:1 to1:85, 95:1 to 1:80, 95:1 to 1:75, 95:1 to 1:70, 95:1 to 1:65, 95:1 to1:60, 95:1 to 1:55, 95:1 to 1:50, 95:1 to 1:45, 95:1 to 1:40, 95:1 to1:35, 95:1 to 1:30, 95:1 to 1:25, 95:1 to 1:20, 95:1 to 1:15, 95:1 to1:10, 95:1 to 1:5, 95:1 to 1:4, 95:1 to 1:3, 95:1 to 1:2, 90:1 to 1:90,90:1 to 1:95, 90:1 to 1:85, 90:1 to 1:80, 90:1 to 1:75, 90:1 to 1:70,90:1 to 1:65, 90:1 to 1:60, 90:1 to 1:55, 90:1 to 1:50, 90:1 to 1:45,90:1 to 1:40, 90:1 to 1:35, 90:1 to 1:30, 90:1 to 1:25, 90:1 to 1:20,90:1 to 1:15, 90:1 to 1:10, 90:1 to 1:5, 90:1 to 1:4, 90:1 to 1:3, 90:1to 1:2, 85:1 to 1:85, 85:1 to 1:95, 85:1 to 1:90, 85:1 to 1:80, 85:1 to1:75, 85:1 to 1:70, 85:1 to 1:65, 85:1 to 1:60, 85:1 to 1:55, 85:1 to1:50, 85:1 to 1:45, 85:1 to 1:40, 85:1 to 1:35, 85:1 to 1:30, 85:1 to1:25, 85:1 to 1:20, 85:1 to 1:15, 85:1 to 1:10, 85:1 to 1:5, 85:1 to1:4, 85:1 to 1:3, 85:1 to 1:2, 80:1 to 1:80, 80:1 to 1:95, 80:1 to 1:90,80:1 to 1:85, 80:1 to 1:75, 80:1 to 1:70, 80:1 to 1:65, 80:1 to 1:60,80:1 to 1:55, 80:1 to 1:50, 80:1 to 1:45, 80:1 to 1:40, 80:1 to 1:35,80:1 to 1:30, 80:1 to 1:25, 80:1 to 1:20, 80:1 to 1:15, 80:1 to 1:10,80:1 to 1:5, 80:1 to 1:4, 80:1 to 1:3, 80:1 to 1:2, 75:1 to 1:75, 75:1to 1:95, 75:1 to 1:90, 75:1 to 1:85, 75:1 to 1:80, 75:1 to 1:70, 75:1 to1:65, 75:1 to 1:60, 75:1 to 1:55, 75:1 to 1:50, 75:1 to 1:45, 75:1 to1:40, 75:1 to 1:35, 75:1 to 1:30, 75:1 to 1:25, 75:1 to 1:20, 75:1 to1:15, 75:1 to 1:10, 75:1 to 1:5, 75:1 to 1:4, 75:1 to 1:3, 75:1 to 1:2,70:1 to 1:70, 70:1 to 1:95, 70:1 to 1:90, 70:1 to 1:85, 70:1 to 1:80,70:1 to 1:75, 70:1 to 1:65, 70:1 to 1:60, 70:1 to 1:55, 70:1 to 1:50,70:1 to 1:45, 70:1 to 1:40, 70:1 to 1:35, 70:1 to 1:30, 70:1 to 1:25,70:1 to 1:20, 70:1 to 1:15, 70:1 to 1:10, 70:1 to 1:5, 70:1 to 1:4, 70:1to 1:3, 70:1 to 1:2, 65:1 to 1:65, 65:1 to 1:95, 65:1 to 1:90, 65:1 to1:85, 65:1 to 1:80, 65:1 to 1:75, 65:1 to 1:70, 65:1 to 1:60, 65:1 to1:55, 65:1 to 1:50, 65:1 to 1:45, 65:1 to 1:40, 65:1 to 1:35, 65:1 to1:30, 65:1 to 1:25, 65:1 to 1:20, 65:1 to 1:15, 65:1 to 1:10, 65:1 to1:5, 65:1 to 1:4, 65:1 to 1:3, 65:1 to 1:2, 60:1 to 1:60, 60:1 to 1:95,60:1 to 1:90, 60:1 to 1:85, 60:1 to 1:80, 60:1 to 1:75, 60:1 to 1:70,60:1 to 1:65, 60:1 to 1:55, 60:1 to 1:50, 60:1 to 1:45, 60:1 to 1:40,60:1 to 1:35, 60:1 to 1:30, 60:1 to 1:25, 60:1 to 1:20, 60:1 to 1:15,60:1 to 1:10, 60:1 to 1:5, 60:1 to 1:4, 60:1 to 1:3, 60:1 to 1:2, 55:1to 1:55, 55:1 to 1:95, 55:1 to 1:90, 55:1 to 1:85, 55:1 to 1:80, 55:1 to1:75, 55:1 to 1:70, 55:1 to 1:65, 55:1 to 1:60, 55:1 to 1:50, 55:1 to1:45, 55:1 to 1:40, 55:1 to 1:35, 55:1 to 1:30, 55:1 to 1:25, 55:1 to1:20, 55:1 to 1:15, 55:1 to 1:10, 55:1 to 1:5, 55:1 to 1:4, 55:1 to 1:3,55:1 to 1:2, 50:1 to 1:95, 50:1 to 1:90, 50:1 to 1:85, 50:1 to 1:80,50:1 to 1:75, 50:1 to 1:70, 50:1 to 1:65, 50:1 to 1:60, 50:1 to 1:55,50:1 to 1:45, 50:1 to 1:40, 50:1 to 1:35, 50:1 to 1:30, 50:1 to 1:25,50:1 to 1:20, 50:1 to 1:15, 50:1 to 1:10, 50:1 to 1:5, 50:1 to 1:4, 50:1to 1:3, 50:1 to 1:2, 45:1 to 1:45, 45:1 to 1:95, 45:1 to 1:90, 45:1 to1:85, 45:1 to 1:80, 45:1 to 1:75, 45:1 to 1:70, 45:1 to 1:65, 45:1 to1:60, 45:1 to 1:55, 45:1 to 1:50, 45:1 to 1:40, 45:1 to 1:35, 45:1 to1:30, 45:1 to 1:25, 45:1 to 1:20, 45:1 to 1:15, 45:1 to 1:10, 45:1 to1:5, 45:1 to 1:4, 45:1 to 1:3, 45:1 to 1:2, 40:1 to 1:40, 40:1 to 1:95,40:1 to 1:90, 40:1 to 1:85, 40:1 to 1:80, 40:1 to 1:75, 40:1 to 1:70,40:1 to 1:65, 40:1 to 1:60, 40:1 to 1:55, 40:1 to 1:50, 40:1 to 1:45,40:1 to 1:35, 40:1 to 1:30, 40:1 to 1:25, 40:1 to 1:20, 40:1 to 1:15,40:1 to 1:10, 40:1 to 1:5, 40:1 to 1:4, 40:1 to 1:3, 40:1 to 1:2, 35:1to 1:35, 35:1 to 1:95, 35:1 to 1:90, 35:1 to 1:85, 35:1 to 1:80, 35:1 to1:75, 35:1 to 1:70, 35:1 to 1:65, 35:1 to 1:60, 35:1 to 1:55, 35:1 to1:50, 35:1 to 1:45, 35:1 to 1:40, 35:1 to 1:30, 35:1 to 1:25, 35:1 to1:20, 35:1 to 1:15, 35:1 to 1:10, 35:1 to 1:5, 35:1 to 1:4, 35:1 to 1:3,35:1 to 1:2, 30:1 to 1:30, 30:1 to 1:95, 30:1 to 1:90, 30:1 to 1:85,30:1 to 1:80, 30:1 to 1:75, 30:1 to 1:70, 30:1 to 1:65, 30:1 to 1:60,30:1 to 1:55, 30:1 to 1:50, 30:1 to 1:45, 30:1 to 1:40, 30:1 to 1:35,30:1 to 1:25, 30:1 to 1:20, 30:1 to 1:15, 30:1 to 1:10, 30:1 to 1:5,30:1 to 1:4, 30:1 to 1:3, 30:1 to 1:2, 25:1 to 1:25, 25:1 to 1:95, 25:1to 1:90, 25:1 to 1:85, 25:1 to 1:80, 25:1 to 1:75, 25:1 to 1:70, 25:1 to1:65, 25:1 to 1:60, 25:1 to 1:55, 25:1 to 1:50, 25:1 to 1:45, 25:1 to1:40, 25:1 to 1:35, 25:1 to 1:30, 25:1 to 1:20, 25:1 to 1:15, 25:1 to1:10, 25:1 to 1:5, 25:1 to 1:4, 25:1 to 1:3, 25:1 to 1:2, 20:1 to 1:95,20:1 to 1:90, 20:1 to 1:85, 20:1 to 1:80, 20:1 to 1:75, 20:1 to 1:70,20:1 to 1:65, 20:1 to 1:60, 20:1 to 1:55, 20:1 to 1:50, 20:1 to 1:45,20:1 to 1:40, 20:1 to 1:35, 20:1 to 1:30, 20:1 to 1:25, 20:1 to 1:15,20:1 to 1:10, 20:1 to 1:5, 20:1 to 1:4, 20:1 to 1:3, 20:1 to 1:2, 15:1to 1:15, 15:1 to 1:95, 15:1 to 1:90, 15:1 to 1:85, 15:1 to 1:80, 15:1 to1:75, 15:1 to 1:70, 15:1 to 1:65, 15:1 to 1:60, 15:1 to 1:55, 15:1 to1:50, 15:1 to 1:45, 15:1 to 1:40, 15:1 to 1:35, 15:1 to 1:30, 15:1 to1:25, 15:1 to 1:20, 15:1 to 1:10, 15:1 to 1:5, 15:1 to 1:4, 15:1 to 1:3,15:1 to 1:2, 10:1 to 1:10, 10:1 to 1:95, 10:1 to 1:90, 10:1 to 1:85,10:1 to 1:80, 10:1 to 1:75, 10:1 to 1:70, 10:1 to 1:65, 10:1 to 1:60,10:1 to 1:55, 10:1 to 1:50, 10:1 to 1:45, 10:1 to 1:40, 10:1 to 1:35,10:1 to 1:30, 10:1 to 1:25, 10:1 to 1:20, 10:1 to 1:15, 10:1 to 1:5,10:1 to 1:4, 10:1 to 1:3, 10:1 to 1:2, 5:1 to 1:5, 5:1 to 1:95, 5:1 to1:90, 5:1 to 1:85, 5:1 to 1:80, 5:1 to 1:75, 5:1 to 1:70, 5:1 to 1:65,5:1 to 1:60, 5:1 to 1:55, 5:1 to 1:50, 5:1 to 1:45, 5:1 to 1:40, 5:1 to1:35, 5:1 to 1:30, 5:1 to 1:25, 5:1 to 1:20, 5:1 to 1:15, 5:1 to 1:10,5:1 to 1:4, 5:1 to 1:3, 5:1 to 1:2, 4:1 to 1:4, 4:1 to 1:95, 4:1 to1:90, 4:1 to 1:85, 4:1 to 1:80, 4:1 to 1:75, 4:1 to 1:70, 4:1 to 1:65,4:1 to 1:60, 4:1 to 1:55, 4:1 to 1:50, 4:1 to 1:45, 4:1 to 1:40, 4:1 to1:35, 4:1 to 1:30, 4:1 to 1:25, 4:1 to 1:20, 4:1 to 1:15, 4:1 to 1:10,4:1 to 1:5, 4:1 to 1:3, 4:1 to 1:2, 3:1 to 1:3, 3:1 to 1:95, 3:1 to1:90, 3:1 to 1:85, 3:1 to 1:80, 3:1 to 1:75, 3:1 to 1:70, 3:1 to 1:65,3:1 to 1:60, 3:1 to 1:55, 3:1 to 1:50, 3:1 to 1:45, 3:1 to 1:40, 3:1 to1:35, 3:1 to 1:30, 3:1 to 1:25, 3:1 to 1:20, 3:1 to 1:15, 3:1 to 1:10,3:1 to 1:5, 3:1 to 1:4, 3:1 to 1:2, 2:1 to 1:2, 2:1 to 1:95, 2:1 to1:90, 2:1 to 1:85, 2:1 to 1:80, 2:1 to 1:75, 2:1 to 1:70, 2:1 to 1:65,2:1 to 1:60, 2:1 to 1:55, 2:1 to 1:50, 2:1 to 1:45, 2:1 to 1:40, 2:1 to1:35, 2:1 to 1:30, 2:1 to 1:25, 2:1 to 1:20, 2:1 to 1:15, 2:1 to 1:10,2:1 to 1:5, 2:1 to 1:4, 2:1 to 1:3.

The compounds of the formula (I) or the active compounds from the classof the pyrethroids with at least one basic centre are capable offorming, for example, acid addition salts, for example with stronginorganic acids such as mineral acids, for example perchloric acid,sulphuric acid, nitric acid, nitrous acid, a phosphorus acid or ahydrohalic acid, with strong organic carboxylic acids such asunsubstituted or substituted, for example halogen-substituted,C₁-C₄-alkanecarboxylic acids, for example acetic acid, saturated orunsaturated dicarboxylic acids, for example oxalic acid, malonic acid,succinic acid, maleic acid, fumaric acid and phthalic acid,hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malicacid, tartaric acid and citric acid, or benzoic acid, or with organicsulphonic acids such as unsubstituted or substituted, for examplehalogen-substituted, C₁-C₄-alkane or arylsulphonic acids, for examplemethane or p-toluenesulphonic acid. The compounds of the formula (I) orthe active compounds from the class of the pyrethroids with at least oneacidic group are capable of forming, for example, salts with bases, forexample metal salts, such as alkali or alkaline-earth metal salts, forexample sodium, potassium or magnesium salts, or salts with ammonia oran organic amine such as morpholine, piperidine, pyrrolidine, a lowermono, di or trialkylamine, for example, ethyl, diethyl, triethyl ordimethylpropylamine, or a lower mono, di or trihydroxyalkylamine, forexample mono, di or triethanolamine. Moreover, if appropriate, it mayalso be possible for corresponding internal salts to be formed. In thecontext of the invention, agrochemically advantageous salts arepreferred. With a view to the close relationship between the compoundsof the formula (I) or the active compounds from the class of thepyrethroids in free form and in the form of their salts, each referenceabove and below to the free compounds of the formula (I) or free activecompounds from the class of the pyrethroids or to their salts is meantto be understood such that this also includes the corresponding saltsand the free compounds of the formula (I) or the free active compoundsfrom the class of the pyrethroids, respectively, if this is applicableand expedient. This also applies in a corresponding manner to tautomersof the compounds of the formula (I) and the active compounds from theclass of the pyrethroids and to their salts.

In the context of the present invention, the term “active compoundcombination” refers to various combinations of compounds of the formula(I) and active compounds from the group of the pyrethroids, for examplein the form of a single ready-mix, in a combined spray mixture composedof separate formulations of the individual active compounds, for examplea tank-mix or in a combined use of the individual active compounds inthe case of their sequential application, for example in successionwithin an appropriate short period of time of, for example, a few hoursor days. According to a preferred embodiment, the order of theapplication of the compounds of the formula (I) and the active compoundsfrom the group of the pyrethroids is not critical for the practice ofthe present invention.

When using the active compound combinations according to the inventionas insecticides and acaricides, the application rates can be variedwithin a relatively wide range, depending on the kind of application.The application rate of the active compound combinations according tothe invention is when treating plant parts, e.g. leaves: from 0.1 to10,000 g/ha, preferably from 10 to 1,000 g/ha, particularly preferablyfrom 50 to 300 g/ha (when the application is carried out by watering ordripping, it may even be possible to reduce the application rate, inparticular when inert substrates such as rock wool or perlite are used);when treating seed: from 2 to 200 g per 100 kg of seed, preferably from3 to 150 g per 100 kg of seed, particularly preferably from 2.5 to 25 gper 100 kg of seed, very particularly preferably from 2.5 to 12.5 g per100 kg of seed; when treating the soil: from 0.1 to 10,000 g/ha,preferably from 1 to 5,000 g/ha.

These application rates are mentioned only by way of example and are notlimiting in the sense of the invention.

The active compound combinations according to the invention can beemployed for protecting plants for a certain period of time aftertreatment against attack by the animal pests mentioned. The period forwhich protection is provided extends generally for 1 to 28 days,preferably for 1 to 14 days, particularly preferably for 1 to 10 days,very particularly preferably for 1 to 7 days after the treatment of theplants with the active compounds, or for up to 200 days after a seedtreatment.

The active compound combinations according to the invention, incombination with good plant tolerance and favourable toxicity towarm-blooded animals and being tolerated well by the environment, aresuitable for protecting plants and plant organs, for increasing theharvest yields, for improving the quality of the harvested material andfor controlling animal pests, in particular insects, arachnids,helminths, nematodes and molluscs, which are encountered in agriculture,in horticulture, in animal husbandry, in forests, in gardens and leisurefacilities, in the protection of stored products and of materials, andin the hygiene sector. They can preferably be used as crop protectioncompositions. They are active against normally sensitive and resistantspecies and against all or some stages of development. Theabovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Anion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus and Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.,Odontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Leucoptera spp., Lithocolletis blancardella, Lithophaneantennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria,Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulemaoryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistiscitrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletiaspp., Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia spp.,Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineolabisselliella, Tortrix viridana, Trichoplusia spp., Tuta spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp. andXenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans and Xiphinema spp.

If appropriate, the active compound combinations according to theinvention can, at certain concentrations or application rates, also beused as herbicides, safeners, growth regulators or agents to improveplant properties, or as microbicides, for example as fungicides,antimycotics, bactericides, viricides (including agents against viroids)or as agents against MLO (Mycoplasma-like organisms) and RLO(Rickettsia-like organisms).

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspoemulsion concentrates, natural compoundsimpregnated with active compound, synthetic substances impregnated withactive compound, fertilizers and also microencapsulations in polymericsubstances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, i.e. liquid solvents, and/or solidcarriers, optionally with the use of surfactants, i.e. emulsifiersand/or dispersants, and/or foam formers. The formulations are producedeither in suitable plants or else before or during application.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical auxiliaries include: extenders, solventsand carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

According to the invention, a carrier is a natural or synthetic, organicor inorganic substance which may be solid or liquid and with which theactive compounds are mixed or bonded for better applicability, inparticular for application to plants or plant parts or seed. The solidor liquid carrier is generally inert and should be suitable for use inagriculture.

Suitable solid or liquid carriers are:

for example ammonium salts and natural rock flours, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and synthetic rock flours, such as finely divided silica, aluminaand silicates; useful solid carriers for granules include: for example,crushed and fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, and also synthetic granules of inorganic andorganic flours, and granules of organic material such as paper, sawdust,coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/orfoam-formers include: for example nonionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; suitabledispersants are nonionic and/or ionic substances, for example from theclasses of the alcohol-POE and/or -POP ethers, acid and/or POP POEesters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts,POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugaradducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl oraryl phosphates or the corresponding PO-ether adducts. Furthermore,suitable oligomers or polymers, for example those derived from vinylicmonomers, from acrylic acid, from EO and/or PO alone or in combinationwith, for example, (poly)alcohols or (poly)amines. It is also possibleto use lignin and its sulphonic acid derivatives, unmodified andmodified celluloses, aromatic and/or aliphatic sulphonic acids and alsotheir adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable oils whichare optionally modified, waxes and nutrients (including tracenutrients), such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability, may also be present.

The active compound content of the use forms prepared from thecommercially available formulations may vary within wide limits. Theactive compound concentration of the use forms is in the range of from0.00000001 to 97% by weight of active compound, preferably in the rangeof from 0.0000001 to 97% by weight, particularly preferably in the rangeof from 0.000001 to 83% by weight or 0.000001 to 5% by weight, and veryparticularly preferably in the range of from 0.0001 to 1% by weight.

The active compound combinations according to the invention can bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with other activecompounds, such as insecticides, attractants, sterilizing agents,bactericides, acaricides, nematicides, fungicides, growth-regulatingsubstances, herbicides, safeners, fertilizers or semiochemicals.

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compound combinations according tothe invention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergist added to be active itself.

When used as insecticides, the active compound combinations according tothe invention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the environment of the plant, on the surface ofparts of plants or in plant tissues.

The compounds are employed in a customary manner appropriate for the useforms.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and plantpopulations, such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can thus beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding the plant varieties which can or cannot be protected byvarietal property rights. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, trunks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes.

The plant parts also include harvested material and also vegetative andgenerative propagation material, for example fruits, seeds, cuttings,tubers, rhizomes, slips, seed, bulbils, layers and runners.

Treatment according to the invention of the plants and plant parts withthe active compound combinations is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

The following plants may be mentioned as plants which can be treatedaccording to the invention: cotton, flax, grapevine, fruit, vegetables,such as Rosaceae sp. (for example pome fruits such as apples and pears,but also stone fruits such as apricots, cherries, almonds and peaches,and soft fruits such as strawberries), Ribesioidae sp., Juglandaceaesp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp.,Oleaceae sp., Actimidaceae sp., Lauraceae sp., Musaceae sp. (for examplebanana plants and banana plantations), Rubiaceae sp. (for examplecoffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for examplelemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes),Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp.,Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for examplecucumber), Alliaceae sp. (for example leeks, onions), Papilionaceae sp.(for example peas); major crop plants such as Gramineae sp. (for examplemaize, turf, cereals such as wheat, rye, rice, barley, oats, millet andtriticale), Asteraceae sp. (for example sunflower), Brassicaceae sp.(for example white cabbage, red cabbage, broccoli, cauliflower, Brusselssprouts, pak choi, kohlrabi, small radishes, and also oilseed rape,mustard, horseradish and cress), Fabacae sp. (for example beans,peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (forexample potatoes), Chenopodiaceae sp. (for example sugar beet, fodderbeet, Swiss chard, beetroot); useful plants and ornamental plants ingardens and forests; and in each case genetically modified types ofthese plants.

The active compound combinations according to the invention areparticularly suitable for the treatment of seed. Here, particularmention may be made of the combinations according to the inventionmentioned above as preferred or particularly preferred. Thus, most ofthe damage to crop plants which is caused by pests occurs as early aswhen the seed is infested during storage and after the seed isintroduced into the soil, and during and immediately after germinationof the plants. This phase is particularly critical since the roots andshoots of the growing plant are particularly sensitive and even minordamage can lead to the death of the whole plant. Protecting the seed andthe germinating plant by the use of suitable compositions is thereforeof particularly great interest.

The control of pests by treating the seed of plants has been known for along time and is the subject of continuous improvements. However, thetreatment of seed entails a series of problems which cannot always besolved in a satisfactory manner. Thus, it is desirable to developmethods for protecting the seed and the germinating plant which dispensewith the additional application of crop protection products after sowingor after emergence of the plants. It is furthermore desirable tooptimize the amount of active compound employed in such a way as toprovide optimum protection for the seed and the germinating plant fromattack by pests, but without damaging the plant itself by the activecompound employed. In particular, methods for the treatment of seedshould also take into consideration the intrinsic insecticidalproperties of transgenic plants in order to achieve optimum protectionof the seed and also of the germinating plant with a minimum of cropprotection products being employed.

Accordingly, the present invention also relates in particular to amethod for protecting seed and germinating plants against attack bypests by treating the seed with an active compound combination accordingto the invention. The method according to the invention for protectingseed and germinating plants against attack by pests comprises a methodwhere the seed is treated simultaneously with an active compound of theformula (I) and one of the pyrethroids 1 to 25. It also comprises amethod where the seed is treated at different times with an activecompound of the formula (I) and one of the pyrethroids 1 to 25. Theinvention also relates to the use of the active compound combinationsaccording to the invention for treating seed for protecting the seed andthe resulting plant against pests. Furthermore, the invention relates toseed treated with an active compound combination according to theinvention for protection against pests. The invention also relates toseed treated simultaneously with an active compound of the formula (I)and one of the pyrethroids 1 to 25. The invention furthermore relates toseed treated at different times with an active compound of the formula(I) and one of the pyrethroids 1 to 25. In the case of seed treated atdifferent times with an active compound of the formula (I) and one ofthe pyrethroids 1 to 25, the individual active compounds of thecomposition according to the invention may be present in differentlayers on the seed. The layers comprising an active compound of theformula (I) and one of the pyrethroids 1 to 25 may optionally beseparated by an intermediate layer. The invention also relates to seedwhere an active compound of the formula (I) and one of the pyrethroids 1to 25 are applied as component of a coating or as a further layer orfurther layers in addition to a coating.

Particular preference is given to using active compound combinationsaccording to the invention comprising at least one compound of theformula (I) selected from the group consisting of the compounds of theformulae (I-1), (I-2), (I-3), (I-4), (I-5), (I-7) and (I-8), andtransfluthrin for treating seed. Particular preference is furthermoregiven to using active compound combinations according to the inventioncomprising at least one compound of the formula (I) selected from thegroup consisting of the compounds of the formulae (I-1), (I-2), (I-3),(I-4), (I-5), (I-6), (I-7) and (I-8), and transfluthrin for treatingtransgenic seed. Particular preference is also given to seed treatedwith an active compound combination comprising at least one compound ofthe formula (I) selected from the group consisting of the compounds ofthe formulae (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7) and (I-8),and transfluthrin. Particular preference is furthermore given to seedtreated simultaneously with an active compound of the formula (I)selected from the group consisting of the compounds of the formulae(I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7) and (I-8), andtransfluthrin. Particular preference is furthermore given to seedtreated at different times with an active compound of the formula (I)selected from the group consisting of the compounds of the formulae(I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7) and (I-8), andtransfluthrin.

One of the advantages of the present invention is that, because of theparticular systemic properties of the active compound combinationsaccording to the invention, treatment of the seed with these activecompound combinations not only protects the seed itself, but also theresulting plants after emergence, from pests. In this manner, theimmediate treatment of the crop at the time of sowing or shortlythereafter can be dispensed with.

A further advantage is the synergistically increased insecticidalactivity of the active compound combinations according to the inventionin comparison with the individual insecticidally active compound, whichexceeds the expected activity of the two active compounds when appliedindividually. Also advantageous is the synergistic enhancement of thefungicidal activity of the active compound combinations according to theinvention compared with the individual fungicidally active compound,which exceeds the expected activity of the active compound appliedindividually. This makes possible an optimization of the amount ofactive compounds employed.

It is likewise to be considered advantageous that the active compoundcombinations according to the invention can be used in particular alsofor transgenic seed, wherein the plants resulting from this seed arecapable of expressing a protein targeted against pests. By treating suchseed with the active compound combinations according to the invention,certain pests can already be controlled by the expression of the, forexample insecticidal, protein, and in addition are saved from damage bythe active compound combinations according to the invention.

The active compound combinations according to the invention are suitablefor protecting seed of any plant variety as already mentioned abovewhich is employed in agriculture, in the greenhouse, in forests or inhorticulture. In particular, this takes the form of seed of maize,peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (forexample sugar beet and fodder beet), rice, millet, wheat, barley, oats,rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes,cabbage species). The active compound combinations according to theinvention are likewise suitable for treating the seed of fruit plantsand vegetables as already mentioned above. The treatment of the seed ofmaize, soya beans, cotton, wheat and canola or oilseed rape is ofparticular importance.

As already mentioned above, the treatment of transgenic seed with anactive compound combination according to the invention is also ofparticular importance. This is the seed of plants comprising generallyat least one heterologous gene which controls the expression of apolypeptide having in particular insecticidal properties. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for treating transgenic seed comprising at leastone heterologous gene originating from Bacillus sp. and whose geneproduct shows activity against the European corn borer and/or theWestern corn rootworm. Particularly preferably, this is a heterologousgene which originates from Bacillus thuringiensis.

Within the context of the present invention, the active compoundcombination according to the invention is applied to the seed eitheralone or in a suitable formulation. Preferably, the seed is treated in astate in which it is stable enough to avoid damage during treatment. Ingeneral, the seed may be treated at any point in time between harvestand sowing. The seed usually used has been separated from the plant andfreed from cobs, shells, stalks, coats, hairs or the flesh of thefruits.

When treating the seed, care must generally be taken that the amount ofthe active compound combination according to the invention applied tothe seed and/or the amount of further additives is chosen in such a waythat the germination of the seed is not adversely affected, or that theresulting plant is not damaged. This must be borne in mind in particularin the case of active compounds which can have phytotoxic effects atcertain application rates.

The compositions according to the invention can be applied directly,i.e. without containing any other components and undiluted. In general,it is preferred to apply the compositions to the seed in the form of asuitable formulation. Suitable formulations and methods for treatingseed are known to the person skilled in the art and are described, forexample, in the following documents: U.S. Pat. No. 4,272,417 A, U.S.Pat. No. 4,245,432 A, U.S. Pat. No. 4,808,430 A, U.S. Pat. No. 5,876,739A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.

The active compounds which can be used in accordance with the inventioncan be converted into the customary seed-dressing formulations, such assolutions, emulsions, suspensions, powders, foams, slurries or othercoating compositions for seed, and also ULV formulations.

These formulations are prepared in a known manner, by mixing the activecompounds with customary additives such as, for example, customaryextenders and also solvents or diluents, colorants, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins and also water.

Colorants which may be present in the seed-dressing formulations whichcan be used in accordance with the invention are all colorants which arecustomary for such purposes. In this context, not only pigments, whichare sparingly soluble in water, but also dyes, which are soluble inwater, may be used. Examples include the dyes known by the namesRhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

Suitable wetting agents which may be present in the seed-dressingformulations which can be used in accordance with the invention are allsubstances which promote wetting and which are conventionally used forthe formulation of agrochemical active compounds. Preference is given tousing alkylnaphthalenesulphonates, such as diisopropyl ordiisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations which can be used in accordance with theinvention are all nonionic, anionic and cationic dispersantsconventionally used for the formulation of agrochemical activecompounds. Preference is given to using nonionic or anionic dispersantsor mixtures of nonionic or anionic dispersants. Suitable nonionicdispersants which may be mentioned are, in particular, ethyleneoxide/propylene oxide block polymers, alkylphenol polyglycol ethers andtristryrylphenol polyglycol ether, and their phosphated or sulphatedderivatives. Suitable anionic dispersants are, in particular,lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehydecondensates.

Antifoams which may be present in the seed-dressing formulations whichcan be used in accordance with the invention are all foam-inhibitingsubstances conventionally used for the formulation of agrochemicalactive compounds. Silicone antifoams and magnesium stearate canpreferably be used.

Preservatives which may be present in the seed-dressing formulationswhich can be used in accordance with the invention are all substanceswhich can be employed for such purposes in agrochemical compositions.Dichlorophen and benzyl alcohol hemiformal may be mentioned by way ofexample.

Secondary thickeners which may be present in the seed-dressingformulations which can be used in accordance with the invention are allsubstances which can be employed for such purposes in agrochemicalcompositions. Cellulose derivatives, acrylic acid derivatives, xanthan,modified clays and finely divided silica are preferred.

Adhesives which may be present in the seed-dressing formulations whichcan be used in accordance with the invention are all customary binderswhich can be employed in seed-dressing products. Polyvinylpyrrolidone,polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned asbeing preferred.

Gibberellins which can be present in the seed-dressing formulationswhich can be used in accordance with the invention are preferably thegibberellins A1, A3 (=gibberellic acid), A4 and A7; gibberellic acid isespecially preferably used. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel” [Chemistryof the Crop Protection Compositions and Pesticides], vol. 2, SpringerVerlag, 1970, pp. 401-412).

The seed-dressing formulations which can be used in accordance with theinvention can be employed for the treatment of a wide range of seed,including the seed of transgenic plants, either directly or afterpreviously having been diluted with water. In this context, additionalsynergistic effects may also occur in cooperation with the substancesformed by expression.

All mixers which can conventionally be employed for the seed-dressingoperation are suitable for treating seed with the seed-dressingformulations which can be used in accordance with the invention or withthe preparations prepared therefrom by addition of water. Specifically,a procedure is followed during the seed-dressing operation in which theseed is placed into a mixer, the specific desired amount ofseed-dressing formulations, either as such or after previously havingbeen diluted with water, is added, and everything is mixed until theformulation is distributed uniformly on the seed. If appropriate, thisis followed by a drying process.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants inwhich a heterologous gene has been stably integrated into the genome.The expression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for exampleantisense technology, cosuppression technology or RNAi technology [RNAinterference]). A heterologous gene that is located in the genome isalso called a transgene. A transgene that is defined by its particularlocation in the plant genome is called a transformation or transgenicevent.

Depending on the plant species or plant varieties, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. For example, the following effects exceedingthe effects actually to be expected are possible: reduced applicationrates and/or a widening of the activity spectrum and/or an increase inthe activity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf colour, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessibility of the harvested products.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are suitable for mobilizing the defence system of theplant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may, if appropriate, be one of thereasons for the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, also those substances or combinations of substanceswhich are capable of stimulating the defence system of plants in such away that, when subsequently inoculated with unwanted phytopathogenicfungi and/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses areunderstood as meaning phytopathogenic fungi, bacteria and viruses. Thus,the substances according to the invention can be employed for protectingplants against attack by the abovementioned pathogens within a certainperiod of time after the treatment. The period within which protectionis brought about generally extends from 1 to 10 days, preferably 1 to 7days, after the treatment of the plants with the active compounds.

Plants and plant varieties which are preferably treated according to theinvention include all plants which have genetic material which impartsparticularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant varieties which are also preferably treated accordingto the invention are resistant against one or more biotic stressfactors, i.e. said plants have a better defence against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant varieties which may also be treated according to theinvention are those plants which are resistant to one or more abioticstress factors. Abiotic stress conditions may include, for example,drought, cold temperature exposure, heat exposure, osmotic stress,waterlogging, increased soil salinity, increased exposure to minerals,exposure to ozone, exposure to strong light, limited availability ofnitrogen nutrients, limited availability of phosphorus nutrients orshade avoidance.

Plants and plant varieties which may also be treated according to theinvention are those plants characterized by enhanced yieldcharacteristics. Enhanced yield in said plants can be the result of, forexample, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including early flowering, flowering control for hybridseed production, seedling vigour, plant size, internode number anddistance, root growth, seed size, fruit size, pod size, pod or earnumber, seed number per pod or ear, seed mass, enhanced seed filling,reduced seed dispersal, reduced pod dehiscence and lodging resistance.Further yield traits include seed composition, such as carbohydratecontent, protein content, oil content and composition, nutritionalvalue, reduction in anti-nutritional compounds, improved processabilityand better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristics of heterosis, or hybrid vigour,which results in generally higher yield, increased vigour, better healthand better resistance towards biotic and abiotic stress factors. Suchplants are typically made by crossing an inbred male-sterile parent line(the female parent) with another inbred male-fertile parent line (themale parent). Hybrid seed is typically harvested from the male-sterileplants and sold to growers. Male-sterile plants can sometimes (e.g. inmaize) be produced by detasseling (i.e. the mechanical removal of themale reproductive organs or male flowers) but, more typically, malesterility is the result of genetic determinants in the plant genome. Inthat case, and especially when seed is the desired product to beharvested from the hybrid plants, it is typically useful to ensure thatmale fertility in hybrid plants, which contain the genetic determinantsresponsible for male sterility, is fully restored. This can beaccomplished by ensuring that the male parents have appropriatefertility restorer genes which are capable of restoring the malefertility in hybrid plants that contain the genetic determinantsresponsible for male sterility. Genetic determinants for male sterilitymay be located in the cytoplasm. Examples of cytoplasmic male sterility(CMS) were for instance described in Brassica species (WO 1992/005251,WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and U.S.Pat. No. 6,229,072). However, genetic determinants for male sterilitycan also be located in the nuclear genome. Male-sterile plants can alsobe obtained by plant biotechnology methods such as genetic engineering.A particularly useful means of obtaining male-sterile plants isdescribed in WO 89/10396 in which, for example, a ribonuclease such as abarnase is selectively expressed in the tapetum cells in the stamens.Fertility can then be restored by expression in the tapetum cells of aribonuclease inhibitor such as barstar (e.g. WO 1991/002069).

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.For example, glyphosate-tolerant plants can be obtained by transformingthe plant with a gene encoding the enzyme5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of suchEPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonellatyphimurium (Comai et al., Science (1983), 221, 370-371), the CP4 geneof the bacterium Agrobacterium sp. (Barry et al., Curr. Topics PlantPhysiol. (1992), 7, 139-145), the genes encoding a petunia EPSPS (Shahet al., Science (1986), 233, 478-481), a tomato EPSPS (Gasser et al., J.Biol. Chem. (1988), 263, 4280-4289) or an Eleusine EPSPS (WO2001/66704). It can also be a mutated EPSPS, as described, for example,in EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995.Glyphosate-tolerant plants can also be obtained by expressing a genethat encodes a glyphosate oxidoreductase enzyme as described in U.S.Pat. No. 5,776,760 and U.S. Pat. No. 5,463,175. Glyphosate-tolerantplants can also be obtained by expressing a gene that encodes aglyphosate acetyltransferase enzyme as described, for example, in WO2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782.Glyphosate-tolerant plants can also be obtained by selecting plantscontaining naturally occurring mutations of the above-mentioned genes asdescribed, for example, in WO 2001/024615 or WO 2003/013226.

Other herbicide-resistant plants are for example plants which have beenmade tolerant to herbicides inhibiting the enzyme glutamine synthase,such as bialaphos, phosphinothricin or glufosinate. Such plants can beobtained by expressing an enzyme detoxifying the herbicide or a mutantglutamine synthase enzyme that is resistant to inhibition. One suchefficient detoxifying enzyme is, for example, an enzyme encoding aphosphinothricin acetyltransferase (such as the bar or pat protein fromStreptomyces species for example). Plants expressing an exogenousphosphinothricin acetyltransferase have been described, for example, inU.S. Pat. No. 5,561,236; U.S. Pat. No. 5,648,477; U.S. Pat. No.5,646,024; U.S. Pat. No. 5,273,894; U.S. Pat. No. 5,637,489; U.S. Pat.No. 5,276,268; U.S. Pat. No. 5,739,082; U.S. Pat. No. 5,908,810 and U.S.Pat. No. 7,112,665.

Further herbicide-tolerant plants are also plants that have been madetolerant to the herbicides inhibiting the enzymehydroxyphenylpyruvatedioxygenase (HPPD).Hydroxyphenyl-pyruvatedioxygenases are enzymes that catalyse thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated HPPD enzyme according to WO 1996/038567, WO1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 1999/034008 and WO 2002/36787. Tolerance of plants toHPPD inhibitors can also be improved by transforming plants with a geneencoding an enzyme prephenate dehydrogenase in addition to a geneencoding an HPPD-tolerant enzyme, as described in WO 2004/024928.

Further herbicide-resistant plants are plants that have been madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitorsinclude, for example, sulphonylurea, imidazolinone, triazolopyrimidines,pyrimidinyl oxy(thio)benzoates, and/orsulphonylaminocarbonyltriazolinone herbicides. Different mutations inthe ALS enzyme (also known as acetohydroxy acid synthase, AHAS) areknown to confer tolerance to different herbicides and groups ofherbicides, as described, for example, in Tranel and Wright, WeedScience (2002), 50, 700-712, and also in U.S. Pat. No. 5,605,011, U.S.Pat. No. 5,378,824, U.S. Pat. No. 5,141,870 and U.S. Pat. No. 5,013,659.The production of sulphonylurea-tolerant plants andimidazolinone-tolerant plants has been described in U.S. Pat. No.5,605,011; U.S. Pat. No. 5,013,659; U.S. Pat. No. 5,141,870; U.S. Pat.No. 5,767,361; U.S. Pat. No. 5,731,180; U.S. Pat. No. 5,304,732; U.S.Pat. No. 4,761,373; U.S. Pat. No. 5,331,107; U.S. Pat. No. 5,928,937;and U.S. Pat. No. 5,378,824; and also in the international publicationWO 1996/033270. Further imidazolinone-tolerant plants have also beendescribed, for example in WO 2004/040012, WO 2004/106529, WO2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO2006/024351 and WO 2006/060634. Further sulphonylurea- andimidazolinone-tolerant plants have also been described, for example inWO 2007/024782.

Other plants tolerant to imidazolinone and/or sulphonylurea can beobtained by induced mutagenesis, by selection in cell cultures in thepresence of the herbicide or by mutation breeding, as described, forexample, for soya beans in U.S. Pat. No. 5,084,082, for rice in WO1997/41218, for sugar beet in U.S. Pat. No. 5,773,702 and WO1999/057965, for lettuce in U.S. Pat. No. 5,198,599 or for sunflower inWO 2001/065922.

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

In the present context, the term “insect-resistant transgenic plant”includes any plant containing at least one transgene comprising a codingsequence encoding:

1) an insecticidal crystal protein from Bacillus thuringiensis or aninsecticidal portion thereof, such as the insecticidal crystal proteinscompiled by Crickmore et al., Microbiology and Molecular Biology Reviews(1998), 62, 807-813, updated by Crickmore et al. (2005) in the Bacillusthuringiensis toxin nomenclature, (online at:http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), orinsecticidal portions thereof, for example proteins of the Cry proteinclasses Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidalportions thereof; or2) a crystal protein from Bacillus thuringiensis or a portion thereofwhich is insecticidal in the presence of a second other crystal proteinfrom Bacillus thuringiensis or a portion thereof, such as the binarytoxin made up of the Cy34 and Cy35 crystal proteins (Moellenbeck et al.,Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environm.Microb. (2006), 71, 1765-1774); or3) a hybrid insecticidal protein comprising parts of two differentinsecticidal crystal proteins from Bacillus thuringiensis, such as ahybrid of the proteins of 1) above or a hybrid of the proteins of 2)above, for example the Cry1A.105 protein produced by maize eventMON98034 (WO 2007/027777); or4) a protein of any one of points 1) to 3) above wherein some,particularly 1 to 10, amino acids have been replaced by another aminoacid to obtain a higher insecticidal activity to a target insectspecies, and/or to expand the range of target insect species affected,and/or because of changes induced in the encoding DNA during cloning ortransformation, such as the Cry3Bb1 protein in maize events MON863 orMON88017, or the Cry3A protein in maize event MIR604; or5) an insecticidal secreted protein from Bacillus thuringiensis orBacillus cereus, or an insecticidal portion thereof, such as thevegetative insecticidal proteins (VIP) listed at:http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html, forexample proteins from the VIP3Aa protein class; or6) a secreted protein from Bacillus thuringiensis or Bacillus cereuswhich is insecticidal in the presence of a second secreted protein fromBacillus thuringiensis or B. cereus, such as the binary toxin made up ofthe VIP1A and VIP2A proteins (WO 1994/21795); or7) a hybrid insecticidal protein comprising parts from differentsecreted proteins from Bacillus thuringiensis or Bacillus cereus, suchas a hybrid of the proteins in 1) above or a hybrid of the proteins in2) above; or8) a protein of any one of points 1) to 3) above wherein some,particularly 1 to 10, amino acids have been replaced by another aminoacid to obtain a higher insecticidal activity to a target insectspecies, and/or to expand the range of target insect species affected,and/or because of changes induced in the encoding DNA during cloning ortransformation (while still encoding an insecticidal protein), such asthe VIP3Aa protein in cotton event COT 102.

Of course, insect-resistant transgenic plants, as used herein, alsoinclude any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected or to delay insect resistance developmentto the plants, by using different proteins insecticidal to the sametarget insect species but having a different mode of action, such asbinding to different receptor binding sites in the insect.

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stress factors. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such stress resistance. Particularly usefulstress-tolerant plants include the following:

a. plants which contain a transgene capable of reducing the expressionand/or the activity of the poly(ADP-ribose)polymerase (PARP) gene in theplant cells or plants, as described in WO 2000/004173 or EP 04077984.5or EP 06009836.5.b. plants which contain a stress tolerance-enhancing transgene capableof reducing the expression and/or the activity of the PARG encodinggenes of the plants or plant cells, as described, for example, in WO2004/090140;c. plants which contain a stress tolerance-enhancing transgene codingfor a plant-functional enzyme of the nicotinamide adenine dinucleotidesalvage biosynthesis pathway, including nicotinamidase, nicotinatephosphoribosyltransferase, nicotinic acid mononucleotideadenyltransferase, nicotinamide adenine dinucleotide synthetase ornicotinamide phosphoribosyltransferase, as described, for example, in EP04077624.7 or WO 2006/133827 or PCT/EP07/002,433.

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as, for example:

1) Transgenic plants which synthesize a modified starch which is alteredwith respect to its chemophysical traits, in particular the amylosecontent or the amylose/amylopectin ratio, the degree of branching, theaverage chain length, the distribution of the side chains, the viscositybehaviour, the gel resistance, the grain size and/or grain morphology ofthe starch in comparison to the synthesized starch in wild-type plantcells or plants, such that this modified starch is better suited forcertain applications. These transgenic plants synthesizing a modifiedstarch are described, for example, in EP 0571427, WO 1995/004826, EP0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/11188, WO1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545,WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654,WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7,WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950,WO 1999/66050, WO 1999/53072, U.S. Pat. No. 6,734,341, WO 2000/11192, WO1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359,U.S. Pat. No. 5,824,790, U.S. Pat. No. 6,013,861, WO 1994/004693, WO1994/009144, WO 1994/11520, WO 1995/35026 and WO 1997/20936.2) Transgenic plants which synthesize non-starch carbohydrate polymersor which synthesize non-starch carbohydrate polymers with alteredproperties in comparison to wild-type plants without geneticmodification. Examples are plants which produce polyfructose, especiallyof the inulin and levan type, as described in EP 0663956, WO1996/001904, WO 1996/021023, WO 1998/039460 and WO 1999/024593, plantswhich produce alpha-1,4-glucans, as described in WO 1995/031553, US2002/031826, U.S. Pat. No. 6,284,479, U.S. Pat. No. 5,712,107, WO1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/14249, plantswhich produce alpha-1,6-branched alpha-1,4-glucans, as described in WO2000/73422, and plants which produce alternan, as described in WO2060/047,727, EP 06077301.7, U.S. Pat. No. 5,908,975 and EP 0728213.3) Transgenic plants which produce hyaluronan, as described, forexample, in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO2007/039316, JP 2006/304779 and WO 2005/012529.

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as cotton plants, with altered fibrecharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants containing a mutation imparting such alteredfibre characteristics and include:

a) plants, such as cotton plants, which contain an altered form ofcellulose synthase genes, as described in WO 1998/000549;b) plants, such as cotton plants, which contain an altered form of rsw2or rsw3 homologous nucleic acids, as described in WO 2004/053219;c) plants, such as cotton plants, with increased expression of sucrosephosphate synthase as described in WO 2001/017333;d) plants, such as cotton plants, with an increased expression ofsucrose synthase, as described in WO 02/45485;

e) plants, such as cotton plants, wherein the timing of theplasmodesmatal gating at the basis of the fibre cell is altered, forexample through downregulation of fibre-selective β-1,3-glucanase asdescribed in WO 2005/017157;

f) plants, such as cotton plants, which have fibres with alteredreactivity, for example through the expression of theN-acetylglucosaminetransferase gene including nodC and chitin synthasegenes, as described in WO 2006/136351.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered oil profile characteristics. Such plants can be obtained bygenetic transformation or by selection of plants containing a mutationimparting such altered oil characteristics and include:

a) plants, such as oilseed rape plants, which produce oil having a higholeic acid content, as described, for example, in U.S. Pat. No.5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or U.S.Pat. No. 6,063,947;b) plants, such as oilseed rape plants, which produce oil having a lowlinolenic acid content, as described in U.S. Pat. No. 6,270,828, U.S.Pat. No. 6,169,190 or U.S. Pat. No. 5,965,755;c) plants, such as oilseed rape plants, which produce oil having a lowlevel of saturated fatty acids, as described, for example, in U.S. Pat.No. 5,434,283.

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins and are the transgenic plants available under thefollowing trade names: YIELD GARD® (for example corn, cotton, soybeans),KnockOut® (for example corn), BiteGard® (for example corn), BT-Xtra®(for example corn), StarLink® (for example corn), Bollgard® (cotton),Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plantswhich may be mentioned are maize varieties, cotton varieties and soyabean varieties which are available under the following trade names:Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soyabeans), Liberty Link® (tolerance to phosphinothricin, for exampleoilseed rape), IMI® (tolerance to imidazolinone) and SCS® (tolerance tosulphonylurea, for example maize). Herbicide-resistant plants (plantsbred in a conventional manner for herbicide tolerance) which may bementioned include the varieties sold under the name Clearfield® (forexample maize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agencies (seefor example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The plants listed can be treated in a particularly advantageous mannerwith the active compound combinations according to the invention. Thepreferred ranges stated above for the active compound combinations alsoapply to the treatment of these plants. Particular emphasis is given tothe treatment of plants with the active compound combinationsspecifically mentioned in the present text.

The active compound combinations according to the invention are not onlyactive against plant pests, hygiene pests and stored-product pests, butalso, in the veterinary medicine sector, against animal parasites(ectoparasites and endoparasites) such as hard ticks, soft ticks, mangemites, harvest mites, flies (stinging and licking), parasitizing flylarvae, lice, hair lice, bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compound combinations according to the invention are alsosuitable for controlling arthropods which attack agricultural livestocksuch as, for example, cattle, sheep, goats, horses, pigs, donkeys,camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees,other domestic animals such as, for example, dogs, cats, caged birds,aquarium fish and so-called experimental animals such as, for example,hamsters, guinea pigs, rats and mice. The control of these arthropods isintended to reduce cases of death and reduced productivity (of meat,milk, wool, hides, eggs, honey etc.), and so more economic and easieranimal husbandry is possible by use of the active compound combinationsaccording to the invention.

The active compound combinations according to the invention are used inthe veterinary sector and in animal husbandry in a known manner byenteral administration in the form of, for example, tablets, capsules,potions, drenches, granules, pastes, boluses, the feed-through processand suppositories, by parenteral administration, such as, for example,by injection (intramuscular, subcutaneous, intravenous, intraperitonealand the like), implants, by nasal administration, by dermal use in theform, for example, of dipping or bathing, spraying, pouring on andspotting on, washing and powdering, and also with the aid of mouldedarticles containing the active compound, such as collars, ear marks,tail marks, limb bands, halters, marking devices and the like.

When used for cattle, poultry, domestic animals and the like, the activecompound combinations can be applied as formulations (for examplepowders, emulsions, flowables) comprising the active compounds in anamount of 1 to 80% by weight, either directly or after 100- to 10000-fold dilution, or they may be used as a chemical dip.

Moreover, it has been found that the active compound combinationsaccording to the invention show a potent insecticidal action againstinsects which destroy industrial materials.

Preferred but nonlimiting examples include the following insects:

beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutes;dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur,termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions.

The ready-to-use compositions may optionally also comprise otherinsecticides, and optionally one or more fungicides.

With respect to possible addition partners for mixing, reference is madeto the insecticides and fungicides mentioned above.

Moreover, the active compound combinations according to the inventioncan be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings,moorings and signalling systems, against fouling.

Furthermore, the active combinations according to the invention can beused alone or in combination with other active compounds as antifoulingcompositions.

The active compound combinations are also suitable for controllinganimal pests in domestic, hygiene and stored-product protection, inparticular insects, arachnids and mites, which are encountered inenclosed spaces, for example dwellings, factory halls, offices, vehiclecabins and the like. They can be used alone or in combination with otheractive compounds and auxiliaries in domestic insecticide products forcontrolling these pests. They are effective against sensitive andresistant species, and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

The use in the field of domestic insecticides takes place alone or incombination with other suitable active compounds such as phosphoricesters, carbamates, neonicotinoids, growth regulators or activecompounds from other known insecticide classes.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orplastic, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The good insecticidal and acaricidal action of the active compoundcombinations according to the invention can be seen from the exampleswhich follow. While the individual active compounds show weaknesses inthe action, the combinations show an action which exceeds a simple sumof actions.

A synergistic effect in insecticides and acaricides is always presentwhen the action of the active compound combinations exceeds the total ofthe actions of the active compounds when applied individually.

The expected action for a given combination of two active compounds canbe calculated according to S. R. Colby, Weeds 15, (1967), 20-22, asfollows:

If

X is the kill rate, expressed in % of the untreated control, when theactive compound A is used at an application rate of m g/ha or in aconcentration of m ppm,

Y is the kill rate, expressed in % of the untreated control, when theactive compound B is used at an application rate of n g/ha or in aconcentration of n ppm,

E is the kill rate, expressed in % of the untreated control, when theactive compounds A and B are used at application rates of m and n g/haor in a concentration of m and n ppm,

then

$E = {X + Y - \frac{X \times Y}{100}}$

If the actual insecticidal or acaricidal kill rate exceeds thecalculated value, the kill of the combination is superadditive, i.e. asynergistic effect is present. In this case, the actually observed killrate must exceed the value calculated using the above formula for theexpected kill rate (E).

EXAMPLES Example A1 Myzus Persicae Test on Cabbage

Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying with theactive compound preparation of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all of the aphids have been killed; 0% means that none of theaphids have been killed. The kill rates determined are entered intoColby's formula (see above).

In this test, for example, the following active compound combinations inaccordance with the present application show a synergistically enhancedactivity compared to the active compounds applied individually:

TABLE A1-1 Myzus persicae test Concentration Kill active compound ing/ha in % after 1^(d) compound (I-4) 4 30 compound (I-5) 0.8 10alpha-cypermethrin 0.16 30 bifenthrin 0.16 20 beta-cyfluthrin 0.16 40cypermethrin 0.8 20 0.16 10 gamma - cyhalothrin 0.16 0 lambda -cyhalothrin 0.032 0 found* calc.** compound (I-4) + alpha- 4 + 0.16 9051 cypermethrin (25:1) according to the invention compound (I-4) +bifenthrin 4 + 0.16 70 44 (25:1) according to the invention compound(I-4) + beta- 4 + 0.16 90 58 cyfluthrin (25:1) according to theinvention compound (I-4) + 4 + 0.8  90 44 cypermethrin (5:1) accordingto the invention compound (I-5) + 0.8 + 0.16   50 19 cypermethrin (5:1)according to the invention compound (I-4) + gamma- 4 + 0.16 80 30cyhalothrin (25:1) according to the invention compound (I-5) + lambda-0.8 + 0.032  30 10 cyhalothrin (25:1) according to the invention *found= activity found **calc. = activity calculated using Colby's formula

TABLE A1-2 Myzus persicae test Concentration Kill Active compound ing/ha in % after 6^(d) compound (I-4) 0.8 0 compound (I-5) 0.8 10 bifenthrin 0.032 0 deltamethrin 0.032 0 found* calc.** compound (I-4) +bifenthrin 0.8 + 0.032 30 10 (25:1) according to the invention compound(I-4) + 0.8 + 0.032 20  0 deltamethrin (25:1) according to the inventioncompound (I-5) + 0.8 + 0.032 50 10 deltamethrin (25:1) according to theinvention *found = activity found **calc. = activity calculated usingColby's formula

Example A2 Myzus Persicae Test on Bell Pepper

Solvent: 7 parts by weight of dimethylformamideEmulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Bell-pepper plants (Capsicum annuum) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying with theactive compound preparation of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all of the aphids have been killed; 0% means that none of theaphids have been killed. The kill rates determined are entered intoColby's formula (see above).

In this test, for example, the following active compound combinations inaccordance with the present application show a synergistically enhancedactivity compared to the active compounds applied individually:

TABLE A2 Myzus persicae test Concentration Kill Active compound in g/hain % after 6^(d) compound (I-5) 0.8 45 transfluthrin 0.8  0 found*calc.** compound (I-5) + transfluthrin 0.8 + 0.8 70 45 (1:1) accordingto the invention *found = activity found **calc. = activity calculatedusing Colby's formula

Example B Phaedon Cochleariae Larvae Test

Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by spraying with theactive ingredient formulation of the desired concentration and populatedwith larvae of the mustard beetle (Phaedon cochleariae) while the leavesare still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed. The kill rates determined are enteredinto Colby's formula (see above).

In this test, the following active compound combination in accordancewith the present application showed a synergistically enhanced activitycompared to the active compounds applied individually:

TABLE B-1 Phaedon cochleariae larvae test Concentration Kill Activecompound in g/ha in % after 2^(d) compound (I-6) 100 0 4 0 compound(I-5) 20 0 bifenthrin 4 67 beta-cyfluthrin 4 83 0.8 50lambda-cyhalothrin 0.16 33 found* calc.** compound (I-6) + bifenthrin100 + 4 83 67 (25:1) according to the invention compound (I-6) + beta-100 + 4 100  83 cyfluthrin (25:1) according to the invention compound(I-5) + beta-   20 + 0.8 83 50 cyfluthrin (25:1) according to theinvention compound (I-6) + lambda-    4 + 0.16 50 33 cyhalothrin (25:1)according to the invention *found = activity found **calc. = activitycalculated using Colby's formula

TABLE B-2 Phaedon cochleariae larvae test Concentration Kill Activecompound in g/ha in % after 6^(d) compound (I-6) 100 0 20 0 compound(I-4) 100 0 20 0 found* calc.** compoung (I-6) + bifenthrin 100 + 4 8367 (25:1) according to the invention compound (I-6) + beta- 100 + 4 100 83 cyfluthrin (25:1) according to the invention compound (I-5) + beta-  20 + 0.8 83 50 cyfluthrin (25:1) according to the invention compound(I-6) + lambda-    4 + 0.16 50 33 cyhalothrin (25:1) according to theinvention *found = activity found **calc. = activity calculated usingColby's formula

Example C Spodoptera Frugiperda Larvae Test

Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being sprayed with thepreparation of active compound of the desired concentration and arepopulated with larvae of the armyworm (Spodoptera frugiperda) while theleaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed. The kill rates determined are enteredinto Colby's formula (see above).

In this test, the following active compound combinations in accordancewith the present application show a synergistically enhanced activitycompared to the active compounds applied individually:

TABLE C-1 Spodoptera frugiperda test Concentration Kill Active compoundin g/ha in % after 2^(d) compound (I-6) 100 0 20 0 compound (I-4) 100 020 0 compound (I-5) 100 0 20 0 deltamethrin 0.8 50 gamma-cyhalothrin 467 lambda-cyhalothrin 4 33 found* calc.** compound (I-6) + deltamethrin20 + 0.8 83 50 (25:1) according to the invention compound (I-4) +deltamethrin 20 + 0.8 67 50 (25:1) according to the invention compound(I-5) + deltamethrin 20 + 0.8 83 50 (25:1) according to the inventioncompound (I-5) + gamma- 100 + 4   100  67 cyhalothrin (25:1) accordingto the invention compound (I-6) + lambda- 100 + 4   83 33 cyhalothrin(25:1) according to the invention compound (I-4) + lambda- 100 + 4   8333 cyhalothrin (25:1) according to the invention compound (I-5) +lambda- 100 + 4   83 33 cyhalothrin (25:1) according to the invention*found = activity found **calc. = activity calculated using Colby'sformula

Example D Tetranychus Urticae Test (Op-Resistant/Spray Treatment)

Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of bean leaves (Phaseolus vulgaris) which are infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aresprayed with an active compound preparation of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all of the spider mites have been killed; 0% means that noneof the spider mites have been killed.

In this test, the following active compound combination in accordancewith the present application showed a synergistically enhanced activitycompared to the active compounds applied individually:

TABLE D-1 Tetranychus urticae test Concentration Kill Active compound ing/ha in % after 2^(d) compound (I-4) 100 0 bifenthrin 4 30lambda-cyhalothrin 4 0 found* calc.** compound (I-4) + deltamethrin100 + 4 50 30 (25:1) according to the invention compound (I-4) + lambda-100 + 4 20  0 cyhalothrin (25:1) according to the invention *found =activity found **calc. = activity calculated using Colby's formula

1. Active compound combinations comprising at least one compound of theformula (I)

in which A represents the 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl,6-bromopyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl,2-chloro-1,3-thiazol-5-yl or 5,6-dichloropyrid-3-yl radical and R¹represents methyl, cyclopropyl, methoxy, 2-fluoroethyl or2,2-difluoroethyl, with the proviso, that4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and4-{[(6-chloropyrid-3-yl)methyl] (cyclopropyl)amino}furan-2(5H)-one areexcluded and at least one compound selected from the group consisting of


2. Active compound combinations according to claim 1, characterized inthat the compound of the formula (I) is selected from the groupconsisting of the compounds of the formulae (I-1), (I-2), (I-3), (I-4),(I-5), (I-6), (I-7) and (I-8).
 3. A method for controlling animal pestscomprising contacting an active compound combination as defined in claim1 with said animal pests.
 4. Method for controlling animal pests,characterized in that an active compound combination as defined in claim1 is allowed to act on animal pests and/or their habitat and/or seed. 5.Method according to claim 4, characterized in that an active compound ofthe formula (I) and one of the pyrethroids 1 to 25 are allowed to act onseed simultaneously.
 6. Method according to claim 4, characterized inthat an active compound of the formula (I) and one of the pyrethroids 1to 25 are allowed to act on seed at different times.
 7. A method fortreating seed comprising contacting active compound combinationaccording to claim 1 with said seed.
 8. A method for treating transgenicplants comprising contacting an active compound combination according toclaim 1 with said transgenic plants.
 9. A method for treating seed oftransgenic plants comprising contacting an active compound combinationaccording to claim 1 with said seed of transgenic plants.
 10. Seedtreated with an active compound combination according to claim
 1. 11.Seed according to claim 10 treated simultaneously with an activecompound of the formula (I) and one of the pyrethroids 1 to
 25. 12. Seedaccording to claim 10 treated at different times with an active compoundof the formula (I) and one of the pyrethroids 1 to 25.